CH142342A - Process for the preparation of an amide of a heterocyclic carboxylic acid. - Google Patents

Process for the preparation of an amide of a heterocyclic carboxylic acid.

Info

Publication number
CH142342A
CH142342A CH142342DA CH142342A CH 142342 A CH142342 A CH 142342A CH 142342D A CH142342D A CH 142342DA CH 142342 A CH142342 A CH 142342A
Authority
CH
Switzerland
Prior art keywords
amide
preparation
hydrogenation
carboxylic acid
carried out
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH142342A publication Critical patent/CH142342A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Description

  

      Verfahren    zur Darstellung eines     Amides    einer     heteroeyeliselien        Carbousäure.       Es wurde gefunden, dass     inan    zu einem       Amid    einer     heterocyclischen        Carbonsäure    ge  langen kann, indem     inan    das     l#Ticotyl-p-plie-          nyläthylainid    hydriert. Als     Hydrierungsmittel     sind zum Beispiel Wasserstoff in Gegenwart  katalytisch wirkender Metalle oder Metall  gemische,     Alkalimetalle    in Gegenwart eines  Alkohols oder Metalle und Säuren zu nennen.

    



  Das     Nipecotyl-,3-pliellylätliylaniid    besteht  aus glasklaren Prismen von unscharfem,     ge-          geil    100   liegendem     Schmelzpunkt.    Es ist in  den meisten organischen Lösungsmitteln lös  lich.     11'6t    Säuren werden leicht lösliche, neu  trale Salze     erhalten.     



  Die neue Verbindung kann entweder  selbst     therapeutische        Verwendung    finden  oder als     Zwischenprodukt    zur Herstellung       pharmazeutischer        Verbindungen    dienen.  



       Beispiel:     78 Teile     Nicotyl-d-pheliyläthylamid    (er  halten durch Zusammenschmelzen     voll        Nieo-          tinsäurechlorid        und    @-Plienyläthylamin-chlor-         hydrat;    Schmelzpunkt<B>82-830)</B> werden mit  300 Teilen     Dekalin    und 15 Teilen Nickel  katalysator unter 40-70 Atmosphären Was  serstoffdruck auf 160-168  erhitzt. Nach  Beendigung der     Wasserstoffaufnahme    wird  der     Autoklaveninhalt    mit Alkohol verdünnt,  der Katalysator     abfiltriert    und das Filtrat  konzentriert.

   Auf Zusatz von etwas Äther  kristallisiert das     Nipecotyl-@-phenyläthylamid     aus.  



  Die Hydrierung gelingt in gleicher Weise  zum Beispiel bei Anwendung von Natrium  und Alkohol oder voll Zink in Gegenwart  einer Säure.



      Process for the preparation of an amide of a heteroeyeliselien carbous acid. It has been found that inan an amide of a heterocyclic carboxylic acid can be obtained by hydrogenating the l # ticotyl-p-plienylethylaamide inanan. Examples of hydrogenating agents that may be mentioned are hydrogen in the presence of catalytically active metals or metal mixtures, alkali metals in the presence of an alcohol or metals and acids.

    



  The nipecotyl-, 3-pliellylätliylaniid consists of crystal-clear prisms with a fuzzy, cool melting point. It is soluble in most organic solvents. Easily soluble, neutral salts are obtained.



  The new compound can either find therapeutic use in its own right or serve as an intermediate for the preparation of pharmaceutical compounds.



       Example: 78 parts of nicotyl-d-pheliylethylamide (obtained by melting together full of nieotinic acid chloride and @ -plienylethylamine chlorohydrate; melting point 82-830) are mixed with 300 parts of decalin and 15 parts of nickel as a catalyst 40-70 atmospheres hydrogen pressure heated to 160-168. After the uptake of hydrogen has ceased, the contents of the autoclave are diluted with alcohol, the catalyst is filtered off and the filtrate is concentrated.

   Upon addition of a little ether, the nipecotyl - @ - phenylethylamide crystallizes out.



  The hydrogenation succeeds in the same way, for example when using sodium and alcohol or full zinc in the presence of an acid.

Claims (1)

PATENTANTSPRUCH Verfahren zur Darstellung eines Amides einer heterocyclischen Carbonsäure, dadurch gekennzeichnet, dass man das Nicoty 1-ss-phe-. nyläthylaniid hydriert. Das Nipecotyl-p-phenyläthylamid besteht aus glasklaren Prismen voll unscharfem, ge- geit 100 liegendem Schmelzpunkt. Es ist in den meisten organischen Lösungsmitteln lös lich. Mit Säuren werden leichtlösliche, neu trale Salze erhalten. PATENT claim Process for the preparation of an amide of a heterocyclic carboxylic acid, characterized in that the Nicoty 1-ss-phe-. nyläthylaniid hydrogenated. The nipecotyl-p-phenylethylamide consists of crystal-clear prisms with a fully indistinct melting point of about 100%. It is soluble in most organic solvents. Easily soluble, neutral salts are obtained with acids. Die neue Verbindung kann entweder selbst tLerape:itische Verwendung finden oder als Zwischenprodukt zur Herstellung pharmazeu tischer Verbindungen dienen. <B>UNTERANSPRÜCHE:</B> I. Ausführungsform des Verfahrens nach Patentanspruch, dadurch gekennzeichnet, dass man die Hydrierung mit Wasserstoff in Gegen art katalytisch wirkender Me talle ausübt. 2. Ausführungsform des Verfahrens nach Patentanspruch, dadurch gekennzeichnet, dass man die Hydrierung mit einem Al kalimetall in Gegenwart eines Alkohols ausübt. 3. The new compound can either find its own therapeutic use or serve as an intermediate for the production of pharmaceutical compounds. SUBClaims: I. Embodiment of the method according to patent claim, characterized in that the hydrogenation is carried out with hydrogen in a counter-type of catalytically active metals. 2. Embodiment of the method according to claim, characterized in that the hydrogenation is carried out with an alkali metal in the presence of an alcohol. 3. Ausführungsform des Verfahrens nach Patentanspruch, dadurch gekennzeichnet, dass man die Hydrierung mit einem reak tionsfähigen Metall in Gegenwart einer Säure ausübt. Embodiment of the process according to claim, characterized in that the hydrogenation is carried out with a reactive metal in the presence of an acid.
CH142342D 1928-07-24 1928-07-24 Process for the preparation of an amide of a heterocyclic carboxylic acid. CH142342A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH142342T 1928-07-24
CH139805T 1928-07-24

Publications (1)

Publication Number Publication Date
CH142342A true CH142342A (en) 1930-09-15

Family

ID=25713398

Family Applications (1)

Application Number Title Priority Date Filing Date
CH142342D CH142342A (en) 1928-07-24 1928-07-24 Process for the preparation of an amide of a heterocyclic carboxylic acid.

Country Status (1)

Country Link
CH (1) CH142342A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4744459A (en) * 1980-12-18 1988-05-17 Ryan Patrick J Method and apparatus for accumulating stockpiles of flowable solid material

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4744459A (en) * 1980-12-18 1988-05-17 Ryan Patrick J Method and apparatus for accumulating stockpiles of flowable solid material

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